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Chapter 38 : Orthosomycins

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Orthosomycins, Page 1 of 2

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Abstract:

The family of orthosomycins includes the everninomicins, which are oligosaccharide antibiotics containing two orthodiester bonds and a dichloroeverninic acid residue. The everninomicins are original antibiotics that belong structurally to the oligosaccharide antibacterial agents. They are characterized by an oligosaccharide structure with the presence of one or more orthodiester-type bonds. This type of bond is unusual in nature but has been described for a series of molecules grouped together in a family known as orthosomycins. Avilamycin is an orthosomycin complex extracted from Tü 57 in 1965. An approach to the structure and activity of everninomicins has been undertaken by means of chemical modifications, particularly of evernimicin. The configuration of the two orthoester bonds at C-49 and C-16 is important for the antibacterial activity. Mechanisms of resistance to evernimicin are complex phenomena which include mainly mutations, methylation, and efflux. Recently it was shown that avilamycin A and evernimicin share common mechanisms of resistance. The gene mutations have been also reported for enterococcal isolates resistant to avilamycin A. The steady-state apparent volume of distribution is on the order of 22 liters, indicating that evernimicin is distributed in the extravascular media. Evernimicin was thought to be an alternative in severe pneumococcal infections for which no other treatment is possible because of a multiresistant strain.

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38

Key Concept Ranking

Antibacterial Agents
1.3358513
Gram-Positive Bacteria
1.1604512
Gram-Negative Bacteria
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Staphylococcus aureus
0.9809407
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Figures

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Figure 1

Everninomicin analogs

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38
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Figure 2

Classification of orthosomycins

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38
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Figure 3

Dichloroeverninic acid

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38
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Figure 4

Everninomicin complex

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38
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Figure 5

Everninomicins

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38
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Figure 6

Evernimicin

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38
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Figure 7

Avilamycin A

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38
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Figure 8

Mutation sites of evernimicin (SCH 27899)

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38
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References

/content/book/10.1128/9781555815929.ch38
1. Banfield CR,, Glue P,, Affrime MB, et al, 1997, Multiple-dose safety, tolerance, and pharmacokinetics of Ziracin® (Sch 27899): a new novel oligosaccharide antibiotic, 37th Intersci Conf Antimicrob Agents Chemother, abstract A-114.
2. Bauernfeind A,, Jungwirth R, 1993, The in vitro activity of everninomicin in comparison with vancomycin and teicoplanin, 33rd Intersci Conf Antimicrob Agents Chemother, abstract 458.
3. Black J,, Calesnick B,, Falco FG,, Weinstein MJ, 1965, Pharmacological properties of everninomicin D, Antimicrob Agents Chemother, p 3846.
4. Boyce JM,, Medeiros AA, 1993, In vitro activity of Sch 27899 against multi-drug resistant gram-positive cocci, 33rd Intersci Conf Antimicrob Agents Chemother, abstract 466.
5. Chin NX,, Neu HC, 1993, In vitro activity of Sch 27899 against aerobic and anaerobic gram-positive Haemophilus influenzae and Moraxella, 33rd Intersci Conf Antimicrob Agents Chemother, abstract 465.
6. Cormican MG,, Marshall SA,, Jones RN, 1995, Preliminary interpretative criteria for disk diffusion susceptibility testing of everninomicin, 35th Intersci Conf Antimicrob Agents Chemother.
7. Ganguly AK,, Pramanik B,, Chan TM,, Sarre O,, Liu YT,, Morton J,, Girijavallabban V, 1989, The structure of new oligosaccharide antibiotics 13-384 components 1 and 5, Heterocycles, 28, 8388.
8. Luedemann GM,, Brodsky BC, 1965, Micromonospora carbonacea sp n, an everninomicin-producing organism, Antimicrob Agents Chemother, 5, 4752.
9. Menon S,, Pai S,, Banfield CR,, Cayen M,, Affrime MB,, Batra V, 1997, Effect of gender on the pharmacokinetics of Ziracin® (Sch 27899) in healthy volunteers, 37th Intersci Conf Antimicrob Agents Chemother, abstract A-113.
10. Nakashio S,, Iwasawa H,, Dun FY,, Kanemitsu K,, Shimada J, 1995, Everninomicin, a new oligosaccharide antibiotic: its antimicrobial activity, post-antibiotic effect and synergistic bactericidal activity, Drugs Exptl Clin Res, 21, 716.
11. Nishino T,, Sakurai M, 1993, In vitro activity of everninomicin (Sch 27899), 33rd Intersci Conf Antimicrob Agents Chemother, abstract 462.
12. Schlaes DM,, Schlaes H,, Etter L,, Hare RS,, Miller GH, 1993, Sch 27899, an everninomicin active against multiply-resistant enterococci and staphylococci, 33rd Intersci Conf Antimicrob Agents Chemother, abstract 460.
13. Urban C,, Mariano N,, Mosinka-Snipas K,, Wadee C,, Chahrour T,, Rahal JJ, 1993, Comparative in vitro activity of Sch 27899, a novel everninomicin, 33rd Intersci Conf Antimicrob Agents Chemother, abstract 463.
14. Vesga O,, Craig WA, 1997, In vivo pharmacodynamic activity of Sch 27899 (Ziracin®), an everninomicin antibiotic, 37th Intersci Conf Antimicrob Agents Chemother, abstract A-32.
15. Weinstein MJ,, Luedemann GM,, Oden EM,, Wagman GH, 1965, Everninomicin, a new antibiotic complex from Micromonospora carbonacea, Antimicrob Agents Chemother, p 2432.

Tables

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Table 1

Physicochemical properties of avilamycin A

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38
Generic image for table
Table 2

Physicochemical properties of evernimicin (SCH 27899)

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38
Generic image for table
Table 3

In vitro activity of evernimicin

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38
Generic image for table
Table 4

Pharmacokinetics of evernimicin at ascending doses

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38
Generic image for table
Table 5

Pharmacokinetics of evernimicin at repeated ascending doses

Citation: Bryskier A. 2005. Orthosomycins, p 983-990. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch38

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